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Lower NY Fun

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You could meet at Bradley International (KBDL) in Windsor Locks, CT. There ia a terrific Air Museum on the airport and there are some nice restaurants nearby.

http://www.neam.org/
 
You didn't say whether you were driving or flying for this meeting.

I would suggest the following in no particular order.

USMA at West Point - beautiful setting overlooking the Hudson. See our tax dollars at work building fine cadets. However, your timing may not be the best because I think everybody will be in Philly for the Army-Navy game.

Ossining, NY - right across the river from West Point roughly is Sing-sing prison. Kind of morose I know but there is a prison museum down the street. I saw an article about that new Texan prison museum - good old Sing-sing has been there for a long time.

Rhinebeck - well your timing is bad on this one, they close the museum at the Old Rhinebeck Aerodrome on Oct 31st each year. Quite a nice little airfield and airshow of "vintage" aircraft. I have no idea if anything is available in the cold weather.

The Catskills - visit Woodstock (yes, that Woodstock) and the beautiful Catskill mountains. Heck if cold and some snow hit, you can go ski Hunter Mountain (with the rest of NY City residents). Warning it could be busy if first snow.

For airports - you have stupid newburgh, er I mean Stewart Newburgh which has nothing of substance to claim except that it was an grand old airbase at one time. Some cool National Guard equipment out there, but nothing to do. You have Poughkeepsie (POU) which used to have the finest airport restaurant in the world known as the Woronack House but alas this has been replaced by a little deli not worth the fuel to get there. Your last choice in airport food up the Hudson is Meadowgreens Restaurant at Columbia County (1B1) if it still exists. Norht end of the airport and a short walk.

OK, I've exhausted my knowledge of the area.
 
How about .....

West Point , Wineries along the hudson ,Franklin Roosevelts Home, Vanderbilt mansion ,Blondies diner in Rhinebeck ( great food for Breakfast) Take the metro north down the hudson to New York city while humming "New York State of Mind" by Billy Joel Once in NYC stop over at the WTC site for some quiet reflection and then hit the village for the best Italian food Bleeker street and Carmine after diner hit Roccos pastries on Bleeker and 6th ave for awesome pastries -Avoid little italy Its too commercial Most of all enjoy yourself!!
 
Sing Sing but no See See

As a native of Ossining, I think I am correct in saying that the prison is entirely useless as a tourist destination. To the best of my knowledge, there are no tours of the property available without prior arrangement (for "scared straight"-type adventures, for instance)... There's not much to see from the outside because of the high walls, and they WILL dispatch some angry-looking individuals with guns to "discourage" you from taking any pictures of the outside walls if you want to record your visit. Trust me on this one, I know from personal fairly recent personal experience.

There IS a part of the Caputo Community Center that is dedicated to the prison, but it is not on the prison grounds... It's located on the main road (Rt. 9) that runs through the middle of town. There's also a portion of the Ossining Historical Society Museum dedicated to the prison, but that is further still from the prison proper.

West Point is a lovely place to visit, though. Contrary to what was posted earlier, it is not directly across the river, however. It is probably 45 minutes away, up the river and on the opposite side. WP is definitely worth a visit.
 

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